WO2002036601A2 - Phase transfer catalyzed glycosidation of an indolocarbazole - Google Patents
Phase transfer catalyzed glycosidation of an indolocarbazole Download PDFInfo
- Publication number
- WO2002036601A2 WO2002036601A2 PCT/US2001/047603 US0147603W WO0236601A2 WO 2002036601 A2 WO2002036601 A2 WO 2002036601A2 US 0147603 W US0147603 W US 0147603W WO 0236601 A2 WO0236601 A2 WO 0236601A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- formula
- compound
- hydroxide
- group
- Prior art date
Links
- 0 *N(C(c(c1c2[n]c3ccccc13)c1c3c2[n]c2ccccc32)=O)C1=O Chemical compound *N(C(c(c1c2[n]c3ccccc13)c1c3c2[n]c2ccccc32)=O)C1=O 0.000 description 1
- RBOCVPFTOFUQLE-UHFFFAOYSA-N CN(C(c(c1c2[nH]c3cc(O)ccc13)c1c3c2[n](C(C(C2O)O)OC(CO)C2O)c2cc(O)ccc32)=O)C1=O Chemical compound CN(C(c(c1c2[nH]c3cc(O)ccc13)c1c3c2[n](C(C(C2O)O)OC(CO)C2O)c2cc(O)ccc32)=O)C1=O RBOCVPFTOFUQLE-UHFFFAOYSA-N 0.000 description 1
- ZQUCGFJVMQSUAZ-UHFFFAOYSA-N O=C(c1c(c(c([nH]2)c3)ccc3OCc3ccccc3)c2c(CCC(C(C(C2OCc3ccccc3)OCc3ccccc3)OC(COCc3ccccc3)C2OCc2ccccc2)c2c-3ccc(OCc4ccccc4)c2)c-3c11)NC1=O Chemical compound O=C(c1c(c(c([nH]2)c3)ccc3OCc3ccccc3)c2c(CCC(C(C(C2OCc3ccccc3)OCc3ccccc3)OC(COCc3ccccc3)C2OCc2ccccc2)c2c-3ccc(OCc4ccccc4)c2)c-3c11)NC1=O ZQUCGFJVMQSUAZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Definitions
- R and Rl are independently: 1) H,
- R5 and R6 are independently:
- R7 i is:
- furanoses include xylofuranose, arabinofuranose, ribofuranose, allofuranose, and 2-deoxyribofuranoses.
- R9 can generally be any known O-protecting group. Examples of such protecting groups include, but are not limited to: benzyl, p-nitrobenzyl, tolyl, and the like. A more preferred protecting group is benzyl (Bn), i.e., CH2Ph. Other suitable protecting groups will be known to those of skill in the art, examples of which can be found in Protective Groups in Organic Synthesis by Peter G. M. Wuts and Theodora W. Greene; John Wiley & Sons, 3 rd ed. (1999).
- the preferred bases for the coupling reaction are alkali hydroxides, such as lithium, sodium, potassium, and cesium hydroxide. Potassium hydroxide and sodium hydroxide are more preferred.
- the base concentration in water can vary from about 5% w/w to about 95% w/w. The more preferred concentrations are about 45% to about 50% w/w.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0302923A HUP0302923A3 (en) | 2000-10-31 | 2001-10-26 | Process for the phase transfer catalyzed glycosidation of indolocarbazole derivatives |
MXPA03003871A MXPA03003871A (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole. |
BR0115036-7A BR0115036A (en) | 2000-10-31 | 2001-10-26 | Process for the preparation of a compound |
NZ525398A NZ525398A (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
US10/415,509 US20040024196A1 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
CA002426815A CA2426815A1 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
AU2894502A AU2894502A (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
EA200300525A EA005209B1 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
KR1020037005897A KR100813086B1 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
PL01365574A PL365574A1 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
IL15554301A IL155543A0 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
AU2002228945A AU2002228945B2 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
JP2002539359A JP3554560B2 (en) | 2000-10-31 | 2001-10-26 | Glycosidation of indolocarbazole using phase transfer catalyst |
EP01990074A EP1333826A2 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
IS6791A IS6791A (en) | 2000-10-31 | 2003-04-16 | Induced phase transport of glycoloside on indolocarbazole |
BG107737A BG107737A (en) | 2000-10-31 | 2003-04-17 | Phase transfer catalyzed glycosidation of an indolocarbazole |
NO20031922A NO20031922L (en) | 2000-10-31 | 2003-04-29 | Phase transfer catalyzed glycosidation of an indolcarbazole |
HK04106904A HK1064053A1 (en) | 2000-10-31 | 2004-09-10 | Process for phase transfer catalyzed glycosidationof an indolopyrrolocarbazole |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24467500P | 2000-10-31 | 2000-10-31 | |
US60/244,675 | 2000-10-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002036601A2 true WO2002036601A2 (en) | 2002-05-10 |
WO2002036601A3 WO2002036601A3 (en) | 2002-11-28 |
Family
ID=22923680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/047603 WO2002036601A2 (en) | 2000-10-31 | 2001-10-26 | Phase transfer catalyzed glycosidation of an indolocarbazole |
Country Status (21)
Country | Link |
---|---|
US (2) | US6555677B2 (en) |
EP (1) | EP1333826A2 (en) |
JP (1) | JP3554560B2 (en) |
KR (1) | KR100813086B1 (en) |
CN (1) | CN1240380C (en) |
AU (2) | AU2894502A (en) |
BG (1) | BG107737A (en) |
BR (1) | BR0115036A (en) |
CA (1) | CA2426815A1 (en) |
CZ (1) | CZ20031209A3 (en) |
EA (1) | EA005209B1 (en) |
HK (1) | HK1064053A1 (en) |
HU (1) | HUP0302923A3 (en) |
IL (1) | IL155543A0 (en) |
IS (1) | IS6791A (en) |
MX (1) | MXPA03003871A (en) |
NO (1) | NO20031922L (en) |
NZ (1) | NZ525398A (en) |
PL (1) | PL365574A1 (en) |
WO (1) | WO2002036601A2 (en) |
ZA (1) | ZA200303198B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005026185A1 (en) * | 2003-09-16 | 2005-03-24 | Banyu Pharmaceutical Co., Ltd. | Novel indolopyrrolocarbazole derivative with antitumor activity |
EP1754711A1 (en) * | 2004-05-28 | 2007-02-21 | Banyu Pharmaceutical Co., Ltd. | Process for producing indolopyrrolocarbazole derivative |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6555677B2 (en) * | 2000-10-31 | 2003-04-29 | Merck & Co., Inc. | Phase transfer catalyzed glycosidation of an indolocarbazole |
WO2005003147A2 (en) | 2003-05-30 | 2005-01-13 | Pharmasset, Inc. | Modified fluorinated nucleoside analogues |
CN101023094B (en) * | 2004-07-21 | 2011-05-18 | 法莫赛特股份有限公司 | Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives |
EP1809301B1 (en) | 2004-09-14 | 2019-11-06 | Gilead Pharmasset LLC | 2-fluoro-2-alkyl-substituted d-ribonolactone intermediates |
US7537774B2 (en) * | 2005-12-23 | 2009-05-26 | Orion Therapeautics, Llc | Therapeutic formulation |
US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
US8173621B2 (en) * | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
US8716263B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
EP3222628A1 (en) | 2008-12-23 | 2017-09-27 | Gilead Pharmasset LLC | Nucleoside phosphoramidates |
US8551973B2 (en) | 2008-12-23 | 2013-10-08 | Gilead Pharmasset Llc | Nucleoside analogs |
US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
TWI576352B (en) | 2009-05-20 | 2017-04-01 | 基利法瑪席特有限責任公司 | Nucleoside phosphoramidates |
PL3290428T3 (en) | 2010-03-31 | 2022-02-07 | Gilead Pharmasset Llc | Tablet comprising crystalline (s)-isopropyl 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2h)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate |
PT3290428T (en) | 2010-03-31 | 2021-12-27 | Gilead Pharmasset Llc | Tablet comprising crystalline (s)-isopropyl 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1 (2h)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate |
AU2011336632B2 (en) | 2010-11-30 | 2015-09-03 | Gilead Pharmasset Llc | Compounds |
US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
EP4005560A1 (en) | 2013-08-27 | 2022-06-01 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4808613A (en) * | 1986-11-21 | 1989-02-28 | Bristol-Myers Company | Rebeccamycin derivative containing pharmaceutical composition |
US5516772A (en) * | 1993-09-16 | 1996-05-14 | Cephalon, Inc. | K-252 derivatives which enhance neurotrophin-induced activity |
US5591842A (en) * | 1991-11-29 | 1997-01-07 | Banyu Pharmaceutical Co., Ltd. | Indolopyrrolocarbazole derivatives |
US5629304A (en) * | 1994-03-18 | 1997-05-13 | Kyowa Hakko Kogyo Co., Ltd. | Therapeutic agent for thrombocytopenia and indolocarbazole derivatives |
WO1998007433A1 (en) * | 1996-08-22 | 1998-02-26 | Bristol-Myers Squibb Company | Cytotoxic amino sugar and related sugar derivatives of indolopyrrolocarbazoles |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8818430D0 (en) * | 1988-08-03 | 1988-09-07 | Tate & Lyle Plc | Process |
NZ245203A (en) | 1991-11-29 | 1997-07-27 | Banyu Pharma Co Ltd | 5h-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6h)-dione derivatives substituted in position-13 by a pentose or hexose group; corresponding indolo-furano(anhydride)intermediates |
US5668271A (en) | 1991-11-29 | 1997-09-16 | Banyu Pharmaceutical Co., Ltd. | Indolopyrrolocarbazole derivatives |
US5437996A (en) | 1992-11-24 | 1995-08-01 | Banyu Pharmaceutical Co., Ltd. | Microtetraspora strain for preparation of indolopyrrolocarbazole derivatives |
US5589365A (en) | 1991-11-29 | 1996-12-31 | Banyu Pharmaceutical Co., Ltd. | Process for producing glycosylated indolopyrrolocarbazole derivatives by culturing certain microorganisms |
US5804564A (en) | 1994-05-09 | 1998-09-08 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
US5922860A (en) * | 1994-05-09 | 1999-07-13 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
FR2750135B1 (en) * | 1996-06-20 | 1998-08-14 | Ceca Sa | CORRESPONDING FLUOROALKYL ACIDS URONIC GLYCOSIDES AND LACTONES-6 (3) |
US6555677B2 (en) * | 2000-10-31 | 2003-04-29 | Merck & Co., Inc. | Phase transfer catalyzed glycosidation of an indolocarbazole |
-
2001
- 2001-10-22 US US10/002,061 patent/US6555677B2/en not_active Expired - Fee Related
- 2001-10-26 NZ NZ525398A patent/NZ525398A/en unknown
- 2001-10-26 HU HU0302923A patent/HUP0302923A3/en unknown
- 2001-10-26 MX MXPA03003871A patent/MXPA03003871A/en active IP Right Grant
- 2001-10-26 CN CNB018214029A patent/CN1240380C/en not_active Expired - Fee Related
- 2001-10-26 EP EP01990074A patent/EP1333826A2/en not_active Withdrawn
- 2001-10-26 AU AU2894502A patent/AU2894502A/en active Pending
- 2001-10-26 JP JP2002539359A patent/JP3554560B2/en not_active Expired - Fee Related
- 2001-10-26 WO PCT/US2001/047603 patent/WO2002036601A2/en active IP Right Grant
- 2001-10-26 EA EA200300525A patent/EA005209B1/en not_active IP Right Cessation
- 2001-10-26 IL IL15554301A patent/IL155543A0/en unknown
- 2001-10-26 AU AU2002228945A patent/AU2002228945B2/en not_active Ceased
- 2001-10-26 KR KR1020037005897A patent/KR100813086B1/en not_active IP Right Cessation
- 2001-10-26 PL PL01365574A patent/PL365574A1/en not_active Application Discontinuation
- 2001-10-26 BR BR0115036-7A patent/BR0115036A/en not_active Withdrawn
- 2001-10-26 US US10/415,509 patent/US20040024196A1/en not_active Abandoned
- 2001-10-26 CZ CZ20031209A patent/CZ20031209A3/en unknown
- 2001-10-26 CA CA002426815A patent/CA2426815A1/en not_active Abandoned
-
2003
- 2003-04-16 IS IS6791A patent/IS6791A/en unknown
- 2003-04-17 BG BG107737A patent/BG107737A/en unknown
- 2003-04-24 ZA ZA200303198A patent/ZA200303198B/en unknown
- 2003-04-29 NO NO20031922A patent/NO20031922L/en not_active Application Discontinuation
-
2004
- 2004-09-10 HK HK04106904A patent/HK1064053A1/en not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4808613A (en) * | 1986-11-21 | 1989-02-28 | Bristol-Myers Company | Rebeccamycin derivative containing pharmaceutical composition |
US5591842A (en) * | 1991-11-29 | 1997-01-07 | Banyu Pharmaceutical Co., Ltd. | Indolopyrrolocarbazole derivatives |
US5516772A (en) * | 1993-09-16 | 1996-05-14 | Cephalon, Inc. | K-252 derivatives which enhance neurotrophin-induced activity |
US5629304A (en) * | 1994-03-18 | 1997-05-13 | Kyowa Hakko Kogyo Co., Ltd. | Therapeutic agent for thrombocytopenia and indolocarbazole derivatives |
WO1998007433A1 (en) * | 1996-08-22 | 1998-02-26 | Bristol-Myers Squibb Company | Cytotoxic amino sugar and related sugar derivatives of indolopyrrolocarbazoles |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005026185A1 (en) * | 2003-09-16 | 2005-03-24 | Banyu Pharmaceutical Co., Ltd. | Novel indolopyrrolocarbazole derivative with antitumor activity |
EP1754711A1 (en) * | 2004-05-28 | 2007-02-21 | Banyu Pharmaceutical Co., Ltd. | Process for producing indolopyrrolocarbazole derivative |
EP1754711A4 (en) * | 2004-05-28 | 2010-06-23 | Banyu Pharma Co Ltd | Process for producing indolopyrrolocarbazole derivative |
Also Published As
Publication number | Publication date |
---|---|
KR100813086B1 (en) | 2008-03-17 |
EA005209B1 (en) | 2004-12-30 |
NO20031922D0 (en) | 2003-04-29 |
ZA200303198B (en) | 2004-04-23 |
EP1333826A2 (en) | 2003-08-13 |
AU2002228945B2 (en) | 2006-02-02 |
IL155543A0 (en) | 2003-11-23 |
BG107737A (en) | 2004-01-30 |
IS6791A (en) | 2003-04-16 |
NO20031922L (en) | 2003-06-27 |
JP3554560B2 (en) | 2004-08-18 |
AU2894502A (en) | 2002-05-15 |
BR0115036A (en) | 2004-02-25 |
NZ525398A (en) | 2004-12-24 |
CA2426815A1 (en) | 2002-05-10 |
WO2002036601A3 (en) | 2002-11-28 |
US20040024196A1 (en) | 2004-02-05 |
HUP0302923A3 (en) | 2005-02-28 |
PL365574A1 (en) | 2005-01-10 |
MXPA03003871A (en) | 2003-07-28 |
CN1240380C (en) | 2006-02-08 |
US20020058803A1 (en) | 2002-05-16 |
CZ20031209A3 (en) | 2003-10-15 |
HK1064053A1 (en) | 2005-01-21 |
CN1482908A (en) | 2004-03-17 |
KR20030082545A (en) | 2003-10-22 |
HUP0302923A2 (en) | 2003-12-29 |
EA200300525A1 (en) | 2003-08-28 |
US6555677B2 (en) | 2003-04-29 |
JP2004513131A (en) | 2004-04-30 |
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